The first synthesis of a nitromethylene-linked c-(l→2)-disaccharide

Tetrahedron Letters

Volumn 40, Issue 15, 1999, Pages 3053-3056

  Pham Huu, Duy Phong ^a   Petrušová, Mária ^a   BeMiller, James N ^b   Petruš, Ladislav ^a  

^a INSTITUTE OF CHEMISTRY   (Slovakia)

^b PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 HEXENAL; ARABINOSE; DISACCHARIDE; MANNOSE; NITROMETHANE; OXIME DERIVATIVE; PYRANOSIDE;

ARTICLE; CARBOHYDRATE SYNTHESIS; CHEMICAL REACTION; CRYSTALLIZATION; DIASTEREOISOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0033537935     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00363-9     Document Type: Article

References (20)

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3. c) Bimwala., R. M.; Vogel, P., J. Org. Chem., 1992, 57, 2076-2083;
4. d) Giese, B.; Hoch, M.; Lamberth, C.; Schmidt, R. R., Tetrahedron Lett., 1988, 29, 1375-1378;
5. e) Sinaÿ, P., Pure & Appl. Chem., 1997, 69, 459-463 and references cited therein.
6. Martin O. R., Lai W., J. Org. Chem., 1990, 55, 5188-5190; J. Org. Chem., 1993, 58, 176-185.
7. Martin O. R., Lai W., J. Org. Chem., 1990, 55, 5188-5190; J. Org. Chem., 1993, 58, 176-185.
8. a) Witczak Z. J., Chhabra R., Chojnacki J., Tetrahedron Lett., 1997, 38, 2215-2218.
9. b) Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M., J. Org. Chem., 1996, 61, 1894-1897.
10. th Bratislava Symposium on Saccharides, Smolenice, Slovakia, September 1997, Pham-Huu, D.-P.; Petrušová, M.; BeMiller J. N.; Petruš, Programme and Abstracts, p. 60.
11. th Bratislava Symposium on Saccharides, Smolenice, Slovakia, September 1997, Pham-Huu, D.-P.; Petrušová, M.; BeMiller J. N.; Petruš, Programme and Abstracts, p. 60.
12. Pham-Huu, D.-P.; Petrušová, M.; BeMiller, J. N.; Köll, P.; Kopf, J.; Petruš, L. Carbohydr. Res., 1998, 306, 45-55.
13. 4) and concetrated to give adducts 3. Flash chromatography (hexane-ethyl acetate 2:1) afforded 3a in 60% yield and a mixture of two other diastereoisomers in 35 % yield. After crystallization from heptane-ethyl acetate (5:1), the mixture afforded 3b in a 24% yield.
14. Pham-Huu, D.-P.; Petrušová, M.; BeMiller, J. N.; Petruš, L.; Köll, P.; Kopf, J. to be published.
15. For references on the TBTH reduction of primary nitro groups to oximes, see a) Pham-Huu, D.-P.; Petrušová, M.; BeMiller J. N.; Petruš, L. Chem. Papers, 1998, 52, 186;
16. b) Pham-Huu, D.-P.; Petrušová, M.; BeMiller J. N.; Petruš, L. Synlett. 1998, 12, 1319.
17. A mixture of 3a (288 mg, 0.5 mmol), TBTH (0.8 ml, 1.5 mmol), and ABCN (20 mg) in benzene (5 ml) was stirred at 80 °C for 5 h. Then the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Flash chromatography of the residue (silica gel) afforded 4 in a 77% yield.
18. 7
19. 12: C, 53.56; H, 7.19; N, 5.00. Found: C, 53.52; H, 7.35; N, 4.79.
20. Detailed NMR study of E and Z isomers of 4 will be the subject of another report.